Volume 21, Number 3, 698-699, DOI: 10.1007/BF00863259

Dependence of the dissociation constants of phenolic steroids on their structures

V. V. Egorova, A. V. Zakharychev and S. N. Ananchenko

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Abstract

1.  The pKprime a values of 10 phenolic steroids were determined. It is shown that the introduction of a Delta8(9)-double bond conjugated with the aromatic A ring increases the degree of ionization of the phenolic hydroxyl group.
2.  It is shown that transition for 17- and 17agr-keto-3-hydroxy-Delta1,3,5(10)-estratrienes to the corresponding 3,17beta- and 3,17agrbeta-dihydroxy compounds as well as from the normal series to the D homoanalogs is accompanied by a decrease in acidity, which may be the result of the distance effect from the D ring to the A ring.
3.  A linear correlation is observed between the chemical oxidation constants (k2) and the dissociation constants (K) of 3,17-dihydroxy-Delta1,3,5(10)-estratrienes, which makes it possible to assume the existence of an interaction between C3 and C17 (C17agr) by means of distance effects from the A ring to the D ring and from the D ring to the A ring.
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 726–728, March, 1972.

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